Esters of aleuritic acid



Patented Aug. l4, 1945 ulllreo STATES PATENT OFFICE William Joseph Sartorl, Brooklyn, N. Y.

No Drawing. Application April 8, 1942, Serial No. 438,119

14 Qlaims. (01.106-182) This invention relates to alkyl esters of aleuritic 16 trihydroxy palmitic acid) and in which R repand to their use as plasticizers for cellulose resents any alkyl group such as methyl, ethyl, others and esters. propyl, butyl, amyl and the like. Melting points The preparation of alkyl aleuritates, has been and structural formulae of some of the esters dedescribed by various workers. (Ber. 5513, 3843-48 5 scribed in this application are given in Table I.

Table I Melting point, 0. Methyl aleuritate, (IIHr-(CHI) l-o 1143114011, 1-0 0 on. 71-72.

OH OH H Ethyl aleurltate, CH(CH;) CHCH(GH )1-C OOCgHp- 66. 5-67. 5

H OH H I Butyl aleuritate, OHl-(CH1)r-CH-OH(CH;) C O 0 C411. 58-59 H OH OH Amyl aleuritate, ([Jiil -(CHfl -CH-CH-(Cfi C O 0 C Hn 60-63 OH H H I (1922) Wiss Veroflentlich siemens -Konzern 10, The l cellulose ether is u n this appli- No. 2, 108-18 (1931). To the best of my knowlcation to define any derivative in which one or edge, however, the use of alkyl aleuritates has not more of the hydroxyl groups of the cellulose have been disclosed as plasticizers for cellulose ethers n replaced y y. y y aralkoxy andesters. The use of alkyl esters of shellac s groups, as in ethyl cellulose, methyl cellulose and resin plasticizers for cellulose ester lacquers ha benzyl cellulose. The term cellulose ester defines been described by Gardner (U. S. 1,910,100), esters of cellulose with both inorganic and organic These shellac esters are esters of shellac resin its. s as cellulose nitrate. lu s t t self, are themselves resinous and polymeric in cellulose mat cellulose p p nat lu s character, and are not to be confused with the butyrate andthe like. pure crystalline compounds obtained by esterify- Any sui le m ho may be mp for 511g aleuritic acid. preparing and purifying these esters. For ex- An object of the present invention is the-prepample, aleuritic acid may be dissolved in a large aratlon of new' esters of aleuritic acid derived excess of the desired alcohol containing 3% a lrom, shellac. A second object is to use these hydrous hydrogen chloride catalyst, and allowed esters as plasticizers for lacquers containing celluto stand until the acid is substantially esterifled.

lose ethers and esters. K third object is to pre- The reaction mixture can then be dissolved in pare compositions, suchas those used for molding d yl ther and the cataly neutralized and *or extrusion containing derivatives of cellulose, any unesterified aleuritic acid extracted by shakwhereln an ester or aleuritic acid is used as a ing the dilute aqueous sodium carbonate. The plastlcizer. Other objects of my invention will desired ester is obtained in substantially pure appear from the following description. 40 forms by evaporating the solvent and recrystal- Thealkyl esters of aleuritic acid may be prelyzing the residual ester from aqueous alcohol.

pared by any suitable method of esterification as, Alternatively the process described by Blann, for example, the Fischer process. These esters Bassford and Bartovics,- in their pending appliare very compatible with cellulose derivatives and cation Shellac ester and method of making furthermore are readily soluble in the usual solsame (Serial No. 443,169), Example 6, may be vents for cellulose ethers and esters. These new employed.

aleuritic acid esters are excellent plasticizers, The esters of aleuritic acids may be incorposoitening agents, or camphor substitutes and may rated in plastic compositions containing cellulose be used to impart pliability. softness and other derivatives and these compositions may be desirable properties to plastics, films, filaments, molded, rolled or extended into any desired shape fibers and the like containing derivatives of cellulose. ing powders incorporating plastic compositions The esters e ced Within this invent bn ay as described above as well as fillers, pigments berepre n y the structural and extenders may be molded under heatand pressure to any desired shape. Filaments, yarns H H and other textile materials may be made from solutions containing organic derivatives of colsuch as sheets, rods, tubes and the like. Moldm parent i is ajeurltig acid 9 0 lulose and an ester of aleuritic acid by extrusion through orifices into an evaporative atmosphere as in dry spinning or into a precipitating bath as in wet spinning.

Solutions containing the cellulose derivative and the ester of aleuritic acid in a volatile solvent and containing, if desired, other plasticizers and resins, may be used as a lacquer for coating metal, wood, paper, leather and other objects, or as an adhesive, as, for example, in the preparation of safety glass, wherein sheets of glass may be bonded together by means of a composition containing a cellulose derivative and an ester of aleuritic acid. The esters of aleuritic acid are particularly servi'ceableas plasticizing agents for lacquers containing cellulose nitrate dissolved in appropriate solvent mixtures and containing resins compatible with cellulose nitrate and, if desired, other plasticizers, pigments,

Table II Parts Cellulose nitrate 50 Ester gum 25 Ethyl acetete 160 Butyl acetate" 20 Ethyl lactate. 10 Ethyl alcohol. 20 350 Butyl alcohoL. '10 oluene 80 Xylene 50 Table III gives the formulae of lacquers A, B, C and D respectively, A being the control, with no plasticizer, B and C lacquers containing commercial plasticizers, and D containing methyl aleuritate, the numerals indicating parts by weight:

Table III A B C D Cellulose nitrate 50 50 50 50 ster gum 25 25 25 Solvent 350 350 350 Dibutyl phthalate 15 Dicyclohexyl phthalate A, l6 Methyl aleuritate 15 The above lacquers must be diluted with a thinner until they all have the same viscosity.

' This result is only a slight change in concentration from that given in Table III. Tin panels are then coated in the lacquer, dried overnight at room temperature and then six days ina 40 C. oven.

Lacquenfilms were prepared according to the formulation in Table III and were evaluated according to the A. S. T. M. designation B522-39P. Films A, Band C when bent over the conical mandrel specified by this test showed peeling and cracking from the largest diameter to the smallest diameter. In evaluating lacquer D methyl aleuritate was used as the plasticizer, there was no sign of peeling r cracking even to the smallest diameter.

Methyl aleuritate is therefore an excellent than films containing comparable amounts ofdibutyl phthalate or dicyclohexyl phthalate.

As many apparently widely different embodiments of this invention may be ma e without departing from the spirit and scope hereof, it is to be understood that I do not 11 it myself to the specific embodiments thereof except as defined in the appended claims. I

Having described my invention, what I claim and desire to secure by Letters Patent, is as follows:

1. A composition of matter containing: a cellulose derivative selected from the group consisting of cellulose ethers and esters; and a lower alkyl aleuritate.

2. A composition of matter containing: a cellulose derivative selected from the group consisting of cellulose ethers and esters; and an ester of aleuritic acid selected from the group consisting of methyl, ethyl, propyl, butyl, and amyl aleuritates.

3. A flexible filament comprising: a cellulose derivative selected from the group consisting of cellulose ethers and esters; and a lower alkyl aleuritate.

4. A flexible film comprising: a cellulose derivative selected from the group consisting of cellulose ethers and esters; and an ester of eleuritic acid selected from the group consisting of methyl, ethyl, propyl, butyl, and amyl aleuritates.

5. A fiber capable of being formed into useful yarns comprising: a cellulose derivative selected from the group consisting of cellulose ethers and esters; and an ester of aleuritic acid selected from the group consisting of methyl, ethyl, propyl, butyl, and amyl aleuritates.

6. A fiber capable of being formed into useful yarns comprising: a cellulose derivative selected from the group consisting of cellulose ethers and esters; and a lower alkyl aleuritate.

7. A lacquer containing: a cellulose derivative selected from the group consisting of cellulose ethers and esters; a solvent; and a lower alkyl aleuritate.

8. A lacquer containing: a cellulose derivative selected from the group consisting of cellulose ethers and esters; a solvent; and an ester of aleuritic acid selected from the group consisting of 1xmethyl, ethyl, propyl, butyl, and amyl aleuri- 9. A lacquer containing: a cellulose ester; a solvent; and a lower alkyl aleuritate.

10. A lacquer containing: a cellulose ester; a solvent; and an ester of aleuritic acid selected from ,the group consisting of methyl, ethyl, propyl, butyl, and amyl aleuritates.

11. A lacquer containing: cellulose nitrate; a solvent; and butyl aleuritate.

12. A lacquer containing: cellulose nitrate; a solvent; and propyl aleuritate.

13. A lacquer containing: cellulose nitrate; a solvent; and ethyl aleuritate.

14. A lacquer containing: cellulose nitrate; a solvent; and an ester of aleuritic acid selected from the group consisting of methyl, ethyl, propyl, butyl, and amyl aleuritate.

'WILLIAM JOSE H SARTORI. 

